Conversion of alkyl and aryl hydroxy compounds producing aldehyde, alcohol and ketone using manganese oxide/nickel oxide/magnesium oxide catalysts

Abstract

Alkyl and aryl hydroxy compounds are converted to aldehydes, alcohols, and ketones in the presence of hydrogen using a catalyst comprised of the oxides of manganese, nickel and magnesium.

I claim: 
     
       1. A process for the dehydrogenation of at least one compound selected from the group consisting of alkyl and cycloalkyl hydroxy compounds, on the hydrogenation of an aryl hydroxy compound, which comprises subjecting said compound to the action of hydrogen under dehydrogenation conditions or hydrogenation conditions, respectively, in the presence of a catalyst comprising the oxides of manganese, nickel and magnesium, wherein the amounts of the oxides, expressed as free metals present, are 5-30, wt. % manganese, 2-25 wt. % nickel, and 50-90 wt. % magnesium. 
     
     
       2. A process according to claim 1 wherein the alkyl or cycloalkyl hydroxy compound is at least one of a primary alcohol and a secondary alcohol, the primary alcohol is represented by the formula ##STR4## wherein R is selected from alkyl and cycloalkyl radicals having 1 to 20 carbon atoms, the secondary alcohol is represented by the formula ##STR5## wherein each R' is selected from alkyl and cycloalkyl radicals having from 1 to 10 carbon atoms, and wherein the aryl hydroxy compound is represented by the formula ##STR6## wherein each R" is selected from hydrogen, alkyl and cycloalkyl radicals having from 1 to 6 carbon atoms. 
     
     
       3. A process according to claim 2 wherein the primary alcohol is at least one selected from the group consisting of ethanol   1-propanol   1-butanol   2-methyl-1-propanol   2-methyl-1-butanol   3-methyl-1-butanol   2,2-dimethyl-1-propanol   2-methyl-1-pentanol   1-hexanol   1-heptanol and   1-dodecanol, wherein the secondary alcohol is at least one selected from the group consisting of     2-propanol   2-butanol   2-pentanol   3-pentanol   3-methyl-2-butanol   2-hexanol   3-hexanol   2,2-dimethyl-3-butanol   2-decanol   3-decanol   2-dodecanol and   3-dodecanol, and wherein the aryl hydroxy compounds is at least one selected from the group consisting of     phenol   o-cresol   m-cresol   p-cresol   2,3-xylenol   2,4-xylenol   2,5-xylenol   2,6-xylenol   3,4-xylenol   3,5-xylenol   2,3,4-trimethylphenol   2,3,5-trimethylphenol   2,3,6-trimethylphenol   2,4,6-trimethylphenol   3,4,5-trimethylphenol   2-ethylphenol   2-hexylphenol   2,4-dihexylphenol   2-methyl-4-ethylphenol and   2-cyclohexylphenol.   
     
     
       4. A process according to claim 1 wherein the respective weights percent are as follows: 10-25; 5-20; and 60-80. 
     
     
       5. A process according to claim 2 wherein 2-methyl-1-butanol is selected as the alkyl hydroxy compound and it is converted to 2-methyl-1-butanal. 
     
     
       6. A process according to claim 2 wherein the alkyl hydroxy compound selected is 2-butanol and it is converted to methyl ethyl ketone. 
     
     
       7. A process according to claim 2 wherein orthocresol is the aryl hydroxy compound selected and it is converted to 2-methylcyclohexanol and 2-methylcyclohexanone. 
     
     
       8. A process according to claim 2 wherein the aryl hydroxy compound selected is m-cresol and it is converted to cis- and trans-methylcyclohexanol. 
     
     
       9. A process according to claim 2 wherein the aryl hydroxy compound selected is p-cresol and it is converted to 4-methylcyclohexanol. 
     
     
       10. A process according to claim 1 wherein the molar ratio of nickel to manganese, expressed as the free metal, is in the range 0.1/1-3/1. 
     
     
       11. A process according to claim 1 wherein the nickel/manganese the molar ratio, expressed as the free metal, is in the range 0.2/-2/1. 
     
     
       12. A process according to claim 1 wherein the operating conditions include a temperature in the approximate range 400°-900° F. and the amount of hydrogen expressed as the mole ratio hydrogen to reactant feed is in the approximate range 1:1 to 20:1 and the pressure is in the approximate range 50-600 psi.